I realize its just a tv show but when it comes to a plot with an elaborate plan I like it better if its plausible.
1) Isn't it a great coincidence that he happens to have help build the prison
2) Isn't it a great coincidence that he is put in the same prison as his brother
3) How is he going to continue the diabetic routine when the doc is already catching on.
4) That screw that he removed with a quarter, most likely would have been seized and much harder to remove
5) The skill of the tattoo artist to hide the plans within another picture seems unearthly
6) You'd think after loosing those pills his morale would be down since they seem to be integral for his escape, yet he doesn't cave under the pressure of a guy holding some garden shears to his toe.
7) How about the lawyer who gives a vid tape to some person claiming to be the defendents GF. If only evidence were that easy to obtain.
8) With the number of heavy hitters in the prison that the main character has pissed off he should be raped, shanked and left for dead in a shower and not necessarily in that order.
9) Oh yeah the brother claiming he need to get high to commit the murder and it looked like he was smoking a joint. Weed won't help you kill anything except a box of twinkies.